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I'm a professional coach and former practicing lawyer, here to help you explore how to become more effective, intentional, and fulfilled in your personal and professional life. Grab a cup of coffee or tea and join me!

Hi, I'm Erin

Have you been thinking about taking the leap into entrepreneurship, but aren’t sure whether to go for it?

Whether it’s a new idea or something you’ve been thinking about for awhile… it’s tough to be stuck in uncertainty about whether to go for it. I know, I’ve been there myself when I was deciding whether to leave my legal career. Even once I was pretty sure I’d love it, I still had to come to the decision to actually go for it.

At first you’re buzzing with ideas and inspiration. Then you start to research, make pro-con lists, maybe talk about the idea with your friends and family. You may start to worry what other people will think, whether they’ll question if it’s wise or how you could possibly walk away from what you’re doing now or encourage you to stay with what you know. Still, the idea keeps coming up for you, pulling you forward toward excitement and inspiration, but you’re just not sure whether to go for it.

I’ve found being stuck in this space of uncertainty can be so draining and suck the joy right out of you. If that’s you right now, here are 3 things to consider doing first.

1. Talk to people who actually work in the field.

It’s easy to hide behind our computer screens and look at other careers as the answer to our problems, but the grass isn’t always greener. Often the more challenging aspects of jobs aren’t so easy to see from the outside. There’s only so much you can tell about a job from day-dreaming about it!

That’s why it can help to actually talk to people who do what you’re considering doing. It sounds so simple but a lot of people don’t do it.

Reach out to some people and ask if they’ll talk to you. People love to talk about what they do! They’re usually happy to pass along their knowledge and perspective, especially if they wish someone would have done that for them when they were starting out.

Be curious. Ask what their work and their life are like. Ask about the good parts as well as the challenges. A great question is what they would change about it if they could change anything. Of course, everyone’s experience is a little different. So, talk to more than just one or two people to get a broader perspective.

2. Engage on the side first and see how it feels.

A great way to get a sense of whether you’d like the work is to try it out on the side, even if it’s just something you could do for free, and see how it feels. For example, if you’re thinking about becoming an interior decorator, could you offer to decorate a few rooms for family members or friends? If you want to get really into it, you could go all out and treat them like a real client!

While you’re engaged in the work, check in with yourself and notice how you feel. Does it light you up? Does it feel like something you couldn’t live without? Or is it not quite as enjoyable as you expected?

Once you get out of your head and actually engage in the activity, it’s much easier to get a sense of whether it’s something you truly would like to do as a job. If you do it and it totally lights you up and is clearly something you could never live another day without doing, that makes the decision a lot less agonizing to make! On the other hand, if it’s not as great as you thought, aren’t you glad you figured that out before going any further?

3. Ask yourself: what am I giving up if I don’t go for it?

If you’re still struggling to make the decision even though you’re truly lit up by it and are pretty sure it feels so right, try this exercise. Sit down in a quiet place without distractions and think or write about what your life will be like 5 years from now if you don’t take the leap (at least in some form, even if it’s a side hustle for now). Put yourself in the present tense 5 years from now or even at the end of your life…

How do you feel? What’s a day in your life like? How does that sit with you? What have you given up by staying where you are? Do you have regret? Can you live with that?

When I was trying to make the decision about whether to leave my legal career, I found it so helpful to talk it through with my own life coach. I gained so much clarity as she asked me challenging questions and helped me get in touch with what was already in my heart. It was very powerful and nothing like the conversations I had with family or friends because she was on the outside and really empowered me to tap into my own inner knowing.

During that time, I also stumbled across the work of Bronnie Ware. After years working in palliative care (helping patients who were going to die), Bronnie wrote about the five most common regrets of the dying. Number one on her list?

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

It hit me like a punch in the gut. For me, I knew I had to go for it and take the leap. I wasn’t sure what the future had in store for me, whether I’d go all in full-time or do it as a side hustle at first for awhile. All I knew was I had to go for it and give it a shot or I’d be that person with regret.

Once the decision was made and I was no longer stuck in that place of indecision over what to do, I felt a huge sense of relief. The weight of making the decision was off my shoulders and I could breathe again and move forward. I felt lighter and truly excited! That was also another indicator I knew it was right.

Ultimately, you’re the only one who can truly know what’s right for you and my hunch is that you do know. Sure, you may not know how every detail will turn out. Maybe you still have some research to do and logistics to figure out, but I hope that by going through these exercises, you’ll have a better sense of what’s true for you.

What strategies have helped you make a big decision like this? Share in the comments below!